The heartland’s summer soundtrack just got a whole lot louder and twangier. The Winstock Country Music Festival has unveiled the first wave of its 2026 lineup, promising a weekend of boot-stomping anthems, heartfelt ballads, and enough beer-tent energy to fuel a thousand tailgates. Headlining the two-day extravaganza on June 19-20 are Luke Bryan and Dierks Bentley—two titans of modern country whose combined hits could fill a jukebox for days. Joining them are special guests Mitchell Tenpenny, Carly Pearce, Maddie & Tae, Easton Corbin, Zach John King, Lauren Watkins, and a slew of rising stars yet to be named. “This is the lineup that dreams are made of,” festival organizer Tom Yantes beamed. “Winstock’s always been about bringing the best of country home to the heartland—raw, real, and ready to party.”
Tickets and camping passes are flying off the digital shelves, with early-bird bundles offering the steal of the season: general admission weekend passes starting at $199, VIP upgrades with private viewing decks for $349, and full-hookup RV sites for epic group campouts at $150 per spot. “We’ve sold out the first 5,000 tickets in under 24 hours,” Yantes revealed, crediting the buzz to Bryan’s recent tour frenzy and Bentley’s bluegrass-infused summer run. “Fans know Winstock isn’t just a show—it’s a family reunion under the stars.” More artists are slated for announcement soon, but with this initial roster, the 32nd annual edition is shaping up to be the festival’s biggest yet, drawing an expected 30,000 revelers per day to the rolling fields of Winsted, Minnesota.
Winstock Country Music Festival isn’t your average music fest—it’s a labor of love born from community grit and a passion for twang. Founded in 1994 by boosters from a local school and parish, it started as a humble fundraiser at a municipal airport to fix a leaky roof and fund community programs. Three decades later, it’s the Upper Midwest’s premier outdoor country blowout, pulling in 12,000-15,000 fans daily across two stages. Organized entirely by over 1,000 volunteers logging thousands of hours, all proceeds support private education, funding scholarships, tech upgrades, and arts programs for Winsted and nearby towns. “It’s not about profit; it’s about purpose,” Yantes said. “Every ticket sold builds a brighter future for our kids.”
The festival grounds, a 100-acre plot near the original airport site, boast a main stage for headliners, a West Stage for up-and-comers, and a labyrinth of campsites that transform into a neon-lit village by night. Gates open Thursday, June 18, for early arrivals to stake tents amid wildflower meadows. Friday kicks off with pre-show beer-tent jams by local bands, and Saturday explodes into full festival mode with national acts at noon and fireworks capping the headliners. Amenities include shaded VIP lounges with local craft brews, family zones with kid-friendly crafts and bounce houses, food trucks serving brisket tacos and funnel cakes, and a silent disco tent for post-set wind-downs. Past editions have featured drone light shows, charity auctions of signed guitars, and over $2 million raised for community causes since the festival’s start.
What makes Winstock unique is its unapologetic heartland vibe—no corporate gloss, just pure country soul. Held in early June, it’s dubbed the “unofficial kickoff to Midwest summer,” drawing fans from the Dakotas to the Driftless Region for sunburns, singalongs, and campfire stories. Veterans rave about the intimacy: even with swelling crowds, you can snag a front-row spot by arriving at dawn, and the volunteer staff—teachers and farmers in flannel—treat you like kin. “I’ve been coming since ’98,” said Sara Kline from nearby Hutchinson. “It’s like a family picnic where the aunts and uncles are superstars.” Past performers include country legends like Alabama, Tim McGraw, Reba McEntire, Brad Paisley, Miranda Lambert, Luke Combs, Alan Jackson, Toby Keith, and Willie Nelson, cementing Winstock’s reputation as a bucket-list destination.
The 2026 headliners, Luke Bryan and Dierks Bentley, are a perfect pairing of fireworks and front-porch wisdom. Bryan, the Georgia-born everyman who’s sold millions of albums, brings a blend of rowdy hooks and road-worn heart. At 49, the “Crash My Party” star, whose debut album spawned No. 1 hits like “A Little More Country Than That” and “Roll with It,” is riding high off a new album and his American Idol judging gig. His recent tour announcement for 2026, including a stop at Indianapolis’ Lucas Oil Stadium, has fans buzzing. Bryan’s Winstock slot—likely closing Saturday night—promises pyrotechnics-laced renditions of “Country Girl (Shake It for Me),” “Huntin’, Fishin’ and Lovin’ Every Day,” and the tear-jerking “Drink a Beer,” a tribute to his late sister. “Winstock feels like home,” Bryan posted on social media, racking up millions of likes. “Can’t wait to loop back to Minnesota with y’all.”
Bentley, the Arizona-raised hitmaker with a knack for bluegrass detours, counters Bryan’s party vibe with soulful swagger. At 50, he’s notched dozens of No. 1s across multiple albums, from early hits like “What Was I Thinkin’” to newer tracks recorded in Colorado’s mountains. A Grand Ole Opry member with influences like Hank Williams Jr. and Merle Haggard, Bentley’s set could feature “5-1-5-0,” “Black,” and the rowdy “Drunk on a Plane.” Fresh off a 2025 summer tour mixing country staples with bluegrass covers, he’s poised to light up Friday night. “Winstock’s volunteer spirit mirrors what country’s about—giving back,” Bentley said in a recent interview. “Honored to ride this ridge with Luke and the crew.”
The special guests elevate the bill to must-see status, blending chart-toppers with fresh talent. Mitchell Tenpenny, the Nashville native with a husky tenor, brings raw edge with hits like “Drunk Me” and “Truth About You,” which have racked up hundreds of millions of streams. His recent album showcases R&B-infused ballads and breakout energy, promising a set that bridges Vince Gill’s soul with modern pop flair. Carly Pearce, the Kentucky firebrand, redefines female empowerment with Grammy-nominated hits from her divorce-inspired albums. Her No. 1 duet “Never Wanted to Be That Girl” and tracks like “What He Didn’t Do” channel Shania Twain and Trisha Yearwood, fresh off opening for major tours. Her Winstock performance will likely be a masterclass in resilience.
Maddie & Tae, the duo of Maddie Font and Taylor Kerr, bring unfiltered joy post-marriage and motherhood. Since skewering bro-country with “Girl in a Country Song,” their gold-certified debut spawned hits like “Fly” and “Shut Up and Fish.” Recent albums deliver vulnerable tracks like “Die From a Broken Heart,” and their set will likely feature harmonious anthems like “Friends Don’t” and “Woman You Got.” Easton Corbin, the Florida traditionalist with a George Strait-esque baritone, rounds out the veterans. His debut No. 1s “A Little More Country Than That” and “Roll with It” and global remix hit “Are You with Me” promise pedal steel weepers and Merle Haggard-inspired grit.
Emerging acts Zach John King and Lauren Watkins add spark. King, a genre-blending phenom with viral social media buzz, fuses hip-hop beats with banjo riffs in tracks like “Midnight Rodeo” and “Heartbreak Highway,” drawing comparisons to Post Malone. Watkins, a 22-year-old Ole Miss grad, channels Miranda Lambert’s bite with smoky, poetic tales of love and loss in her debut album, fresh off touring with major acts. Her songs like “Burnin’ the Bridge” scream breakout potential.
The festival’s social media buzz is electric, with fans posting under #Winstock26. Comments like “Luke + Dierks + Carly? My liver’s quaking” are racking up thousands of likes, while fan forums dissect dream setlists, hoping for Maddie & Tae’s Disney-inspired energy or Pearce’s heartbreak anthems. TikTok is flooded with fans recreating Pearce’s ballads or King’s viral hits. Critics are calling it a masterclass in heartland harmony, praising the volunteer ethos amid rising ticket prices elsewhere. Winsted’s local economy expects a $5 million boost, from motel sellouts to farm-fresh merch stands.
As camping spots dwindle—full-hookup sites are 70% gone—organizers urge fans to act fast: “Secure your spot before the loop closes.” More artists are coming, but this lineup is a love letter to country’s core: unity, grit, and glory. In Winsted’s fields, under Minnesota skies, Winstock 2026 isn’t just a festival—it’s a family, forged in song. Grab your tickets, pack the cooler, and get ready to make memories that echo like a steel guitar’s cry.
Harlan Reeves covers country festivals for Heartland Harmony, from Nashville’s neon to Midwest meadows. Follow him on social media for lineup updates and live dispatches.
